4-Methoxyphenol → Ethyl 2,2-bis(4-methoxyphenoxy)-acetate

HRID 28113

Reaction equation

HRID 28113 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.Cl[CH:12](Cl)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C.C(OCC)C>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:12]([O:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 90154-MethoxyphenolHCID 10808Ethyl dichloroacetateHCID 5360545Sodium

Product 1

HCID 23338925Ethyl 2,2-bis(4-methoxyphenoxy)-acetateYield 76.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent4×HCID 3283Diethyl EtherSolvent

Procedure

Sodium (5.4 g) is dissolved in absolute ethanol (160 cc). 4-Methoxyphenol (29.2 g) dissolved in absolute ethanol (20 cc) is added. The mixture is stirred for 1 hour at ambient temperature. Ethyl 2,2-dichloro-acetate (20 g) dissolved in absolute ethanol (20 cc) is then added and the mixture is heated under reflux for 20 hours. The ethanol is driven off under reduced pressure (20 mmHg) at 40° C. and the residue is taken up in diethyl ether (100 cc). The organic phase is washed with 0.1 N sodium hydroxide solution (100 cc) and with water (2×100 cc) and is then dried over sodium sulphate, filtered and concentrated to dryness under reduced pressure (20 mmHg) at 40° C. Ethyl 2,2-bis(4-methoxyphenoxy)-acetate (30 g) is thus obtained in the form of an oil.

Workup

  1. additionis added
  2. additionis then added
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 20 hours
  5. customis driven off under reduced pressure (20 mmHg) at 40° C.
  6. washThe organic phase is washed with 0.1 N sodium hydroxide solution (100 cc) and with water (2×100 cc)
  7. dry with materialis then dried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under reduced pressure (20 mmHg) at 40° C

Sources & evidence

ORD record
ord-35ec60e01e794f74b58a8468a258b6f8
Source dataset
uspto-grants-1980_09
Patent number
US04225589

Linked notes

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